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(S)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure

(S)-Flurbiprofen Struktur
51543-39-6
CAS-Nr.
51543-39-6
Bezeichnung:
(S)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure
Englisch Name:
(S)-Flurbiprofen
Synonyma:
CS-1959;C1sH13FO2;d-Flurbiprofen;Esflurbiprofen;Dexflurbiprofen;(S)-FLURBIPROFEN;(+)-Flurbiprofen;(S)-2-Flurbiprofen;(S)-(+)-FLURBIPROFEN;Flurbiprofen (S)-Isomer
CBNumber:
CB8284910
Summenformel:
C15H13FO2
Molgewicht:
244.26
MOL-Datei:
51543-39-6.mol
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(S)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure Eigenschaften

Schmelzpunkt:
109-110 °C(lit.)
Siedepunkt:
376.2±30.0 °C(Predicted)
Dichte
1.199±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,Room Temperature
Löslichkeit
insoluble in H2O; ≥10.9 mg/mL in DMSO; ≥69.1 mg/mL in EtOH
Aggregatzustand
A crystalline solid
pka
4.14±0.10(Predicted)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher T
R-Sätze: 25
S-Sätze: 36/37/39-45
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung GHS hazard pictogramssrc="/GHS06.jpg" width="20" height="20" /> P264, P270, P301+P310, P321, P330,P405, P501
Sicherheit
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P405 Unter Verschluss aufbewahren.
P501 Inhalt/Behälter ... (Entsorgungsvorschriften vom Hersteller anzugeben) zuführen.

(S)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R25:Giftig beim Verschlucken.

S-Sätze Betriebsanweisung:

S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).

Beschreibung

(S)-Flurbiprofen is the COX-active enantiomer of the non-selective COX inhibitor flurbiprofen with IC50 values of 0.48 and 0.47 μM for COX-1 and COX-2, respectively, in guinea pig whole blood. It inhibits the release of 6-keto prostaglandin F1α (6-keto-PGF1α; ) and thromboxane B2 (TXB2; ) from rat whole blood, gastric mucosa, lung, and jejunal tissue ex vivo in a dose-dependent manner. (S)-Flurbiprofen (1 nM) inhibits basal and bradykinin-, serotonin-, and histamine-stimulated prostaglandin E2 (PGE2) release from isolated skin flaps of rat lower hind paws. It also inhibits release of the neuroinflammatory marker calcitonin gene-related peptide (CGRP; Item Nos. 24405 | 24725 | 24728) when used at a concentration of 1 μM. In vivo, (S)-flurbiprofen reduces the number of flinches per minute in the formalin test in rats, indicating antinociceptive activity.

Verwenden

(S)-Flurbiprofen is the S-isomer of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic.

Synthese

The synthesis began with conversion of commercially available aniline 168 to racemic flurbiprofen (169) through a Sandmeyer reaction and subsequent phenyl group introduction through the use of sodium tetraphenylborate. A chiral resolution was then performed on the resulting stereogenic acid on multikilogram scale by treatment with (S)- 1-phenylethylamine in MeOH/toluene, which gave various yields of salt 170 as reported by the authors. Acidification with aqueous HCl delivered (S)-flurbiprofen (XXI). Importantly, with respect to green chemistry considerations, the (R)- enantiomer could be recycled by racemizing the undesired (R)- enantiomer 171 in refluxing methanolic sulfuric acid, improving the overall atom economy of the process and significantly reducing waste.

Synthesis_51543-39-6

(S)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte

(S)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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51543-39-6((S)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure)Verwandte Suche:

Flurbiprofen Acipimox (R)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure (±)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure 4-Biphenylessigsaeure 3-Fluorphenylessigsure (S)-2-Fluor-α-methyl[1,1'-biphenyl]-4-essigsure
  • (S)-(+)-FLURBIPROFEN
  • (S)-FLURBIPROFEN
  • (S)-(+)-2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID
  • Esflurbiprofen
  • (S)-2-fluoro-alpha-methyl[1,1'-biphenyl]-4-acetic acid
  • (S)-(+)-2-Fluoro-α-methyl-4-biphenylacetic acid
  • [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, (S)-
  • [1,1'-Biphenyl]-4-acetic acid, 2-fluoro-α-methyl-, (αS)-
  • d-Flurbiprofen
  • (S)-2-(2-Fluoro-1,1'-biphenyl-4-yl)propionic acid
  • (S)-3-Fluoro-α-methyl-4-phenylbenzeneacetic acid
  • (S)-(+)-2-Fluoro-alpha-methyl-4-biphenylacetic acid (Flurbiprofe
  • 2S)-2-(2-Fluoro-4-biphenyl)propanoic acid
  • Dexflurbiprofen
  • (S)-(+)-2-FLUORO-ALPHA-METHYL-4-BIPHENYLACETIC ACID (FLURBIPROFEN)
  • (S)-2-Flurbiprofen
  • [1,1'-Biphenyl]-4-aceticacid, 2-fluoro-a-methyl-,(aS)-
  • (S)-2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoic acid
  • BTS-24332,SFPP,TT-063,Esflurbiprofen
  • (S)-2-(2-Fluorobiphenyl-4-yl)propanoic acid
  • CS-1959
  • Flurbiprofen (S)-Isomer
  • (S)-Flurbiprofen USP/EP/BP
  • CS-O-34753Q: What is CS-O-34753 Q: What is the CAS Number of CS-O-34753
  • (S)-Flurbiprofen，Esflurbiprofen
  • (+)-Flurbiprofen
  • Prostaglandin E synthase,PGE synthase,Cyclooxygenase,COX,(S)-Flurbiprofen,(S) Flurbiprofen,Inhibitor,inhibit,(S)Flurbiprofen
  • C1sH13FO2
  • (S)-2-(2-Fluoro-[1,1'-biphenyl]-4-yl)propanoic acid
  • 51543-39-6
  • C15H13O2F
  • C6H5C6H3FCHCH3CO2H
  • Chiral Building Blocks
  • Asymmetric Synthesis
  • Carboxylic Acids
  • Organic Building Blocks
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